Acetic Acid → 4-Piperazin-1-yl-7-(trifluoromethyl)quinoline

HRID 333984

Reaktionsgleichung

Reaktionsgleichung von HRID 333984
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([C:12]([F:15])([F:14])[F:13])=[CH:9][CH:10]=2)[N:5]=[CH:4][CH:3]=1.[NH:16]1[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]1.C(O)(=O)C>COCCCOCCCO>[N:16]1([C:2]2[C:11]3[C:6](=[CH:7][C:8]([C:12]([F:15])([F:14])[F:13])=[CH:9][CH:10]=3)[N:5]=[CH:4][CH:3]=2)[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]1

Komponenten

5

Edukt 3

HCID 176Acetic AcidHCID 4837PiperazineHCID 676684-Chloro-7-(trifluoromethyl)quinoline

Produkt 1

HCID 114602054-Piperazin-1-yl-7-(trifluoromethyl)quinolineAusbeute 43 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 669843-(3-Methoxypropoxy)-1-propanolLösungsmittel

Versuchsvorschrift

4-Chloro-7-(trifluoromethyl)quinoline (2.3 g, 10 mmol) was dissolved in dipropyleneglycolmonomethyl ether (10 ml) together with piperazine (6.8 g, 0.1 mol) and glacial acetic acid (0.3 ml) and heated at reflux for 2 days. The mixture was concentrated under reduced pressure and the residue was purified by column chromatography (silica, gradient from ethylacetate to methanol containing 1% ammonia) to yield a yellow crystalline solid (1.2 g, 43%).

Aufarbeitung

  1. temperatureheated
  2. temperatureat reflux for 2 days
  3. concentrationThe mixture was concentrated under reduced pressure
  4. customthe residue was purified by column chromatography (silica, gradient from ethylacetate to methanol containing 1% ammonia)

Quellen und Nachweise

ORD-Eintrag
ord-36a1968ea7154fce9d8ee341c05eb17a
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08883791B2

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